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Der A2+‐Mechanismus der säurekatalytischen Hydrolyse von Epoxiden und anderen cyklischen Oxa‐ Verbindungen
Author(s) -
Willi Alfred V.
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560635
Subject(s) - chemistry , carbonium ion , epoxide , protonation , catalysis , acid catalysis , medicinal chemistry , solvent , hydrolysis , stereochemistry , ion , organic chemistry
It is suggested that the acid catalyzed hydrolyses of isobutene oxide and propene oxide proceed via rate‐determining bimolecular reaction between a carbonium ion and solvent water (A2 + mechanism). The carbonium ion is formed by ring opening of the protonated epoxide, in a relatively fast preceding step. This mechanism is in agreement with all experimental facts known today. There is evidence for a similar mechanism in the acid catalyzed hydrolyses of cyclic acetals.